NP-MRD: Showing NP-Card for Orsellinaldehyde (NP0010751)

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Record Information

Version

2.0

Created at

2021-01-05 20:36:29 UTC

Updated at

2021-07-15 17:06:58 UTC

NP-MRD ID

NP0010751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Orsellinaldehyde

Provided By

NPAtlas

Description

2,4-Dihydroxy-6-methylbenzaldehyde, also known as O-orsellinaldehyde or 2-formyl-5-hydroxy-3-methylphenol, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. 2,4-Dihydroxy-6-methylbenzaldehyde is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Orsellinaldehyde is found in Agrocybe praecox, Aspergillus nidulans and Grifola frondosa. Orsellinaldehyde was first documented in 2006 (PMID: 17002422). Based on a literature review a small amount of articles have been published on 2,4-dihydroxy-6-methylbenzaldehyde (PMID: 29895730) (PMID: 29867500) (PMID: 30269491).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107403D          

 19 19  0  0  0  0            999 V2000
   -1.7861   -1.6420   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5671   -0.7668   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082   -1.2975   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8473   -0.5304   -0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1283   -1.0661   -0.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7099    0.8455   -0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506    1.3935   -0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085    2.7662    0.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6853    0.6130    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095    1.2279    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0623    0.5719    0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280   -1.4251   -0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -2.6829    0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2900   -1.4751    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254   -2.3817   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -1.2820    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6039    1.4686   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354    3.3438    0.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672    2.3189    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9  2  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  3 15  1  0  0  0  0
  5 16  1  0  0  0  0
  6 17  1  0  0  0  0
  8 18  1  0  0  0  0
 10 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C(C([H])=O)C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c1-5-2-6(10)3-8(11)7(5)4-9/h2-4,10-11H,1H3

> <INCHI_KEY>
LJFQTUKKYWDRAT-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.149

> <EXACT_MASS>
152.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.984768614685056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4-dihydroxy-6-methylbenzaldehyde

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
2.242038906666667

> <ALOGPS_LOGS>
-1.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.256552931937074

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.51309032760043

> <JCHEM_PKA_STRONGEST_BASIC>
-5.6973135234019425

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
41.644999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-dihydroxy-6-methylbenzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.786  -1.642  -0.031  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.567  -0.767  -0.059  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.708  -1.298  -0.155  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.847  -0.530  -0.183  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.128  -1.066  -0.279  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.710   0.846  -0.113  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.451   1.393  -0.017  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.309   2.766   0.054  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.685   0.613   0.011  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.010   1.228   0.113  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.062   0.572   0.141  0.00  0.00           O+0
HETATM   12  H   UNK     0      -2.428  -1.425  -0.890  0.00  0.00           H+0
HETATM   13  H   UNK     0      -1.419  -2.683   0.002  0.00  0.00           H+0
HETATM   14  H   UNK     0      -2.290  -1.475   0.957  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.825  -2.382  -0.211  0.00  0.00           H+0
HETATM   16  H   UNK     0       3.596  -1.282   0.594  0.00  0.00           H+0
HETATM   17  H   UNK     0       2.604   1.469  -0.134  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.135   3.344   0.034  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.067   2.319   0.166  0.00  0.00           H+0
CONECT    1    2   12   13   14                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   16                                                       
CONECT    6    4    7   17                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   18                                                       
CONECT    9    7   10    2                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10                                                            
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    3                                                            
CONECT   16    5                                                            
CONECT   17    6                                                            
CONECT   18    8                                                            
CONECT   19   10                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Formyl-5-hydroxy-3-methylphenol	ChEBI
2-Methyl-4,6-dihydroxybenzaldehyde	ChEBI
4-Formyl-5-methylbenzene-1,3-diol	ChEBI
4-Formyl-5-methylresorcinol	ChEBI
6-Methyl-beta-resorcyladehyde	ChEBI
O-Orsellinaldehyde	ChEBI
Orcinaldehyde	ChEBI
Orcylaldehyde	ChEBI
Orsellinaldehyde	ChEBI
6-Methyl-b-resorcyladehyde	Generator
6-Methyl-β-resorcyladehyde	Generator

Chemical Formula

C₈H₈O₃

Average Mass

152.1490 Da

Monoisotopic Mass

152.04734 Da

IUPAC Name

2,4-dihydroxy-6-methylbenzaldehyde

Traditional Name

2,4-dihydroxy-6-methylbenzaldehyde

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(O)=C1C=O

InChI Identifier

InChI=1S/C8H8O3/c1-5-2-6(10)3-8(11)7(5)4-9/h2-4,10-11H,1H3

InChI Key

LJFQTUKKYWDRAT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agrocybe praecox	LOTUS Database	35616633
Aspergillus nidulans	NPAtlas	22510154
Grifola frondosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Hydroxybenzaldehydes

Alternative Parents

Substituents

Hydroxybenzaldehyde
Resorcinol
M-cresol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.12	ALOGPS
logP	2.24	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	7.51	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	41.64 m³·mol⁻¹	ChemAxon
Polarizability	14.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA017284

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

220511

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

155863

Good Scents ID

Not Available

References

General References

Kalvo D, Menkis A, Broberg A: Secondary Metabolites from the Root Rot Biocontrol Fungus Phlebiopsis gigantea. Molecules. 2018 Jun 12;23(6). pii: molecules23061417. doi: 10.3390/molecules23061417. [PubMed:29895730 ]
Lin JT, Liu WH: o-Orsellinaldehyde from the submerged culture of the edible mushroom Grifola frondosa exhibits selective cytotoxic effect against Hep 3B cells through apoptosis. J Agric Food Chem. 2006 Oct 4;54(20):7564-9. doi: 10.1021/jf0616762. [PubMed:17002422 ]
Yong T, Chen S, Xie Y, Shuai O, Li X, Chen D, Su J, Jiao C, Liang Y: Hypouricemic Effects of Extracts From Agrocybe aegerita on Hyperuricemia Mice and Virtual Prediction of Bioactives by Molecular Docking. Front Pharmacol. 2018 May 15;9:498. doi: 10.3389/fphar.2018.00498. eCollection 2018. [PubMed:29867500 ]
Tomas-Hernandez S, Garcia-Vallve S, Pujadas G, Valls C, Ojeda-Montes MJ, Gimeno A, Cereto-Massague A, Roca-Martinez J, Suarez M, Arola L, Blanco J, Mulero M, Beltran-Debon R: Anti-inflammatory and Proapoptotic Properties of the Natural Compound o-Orsellinaldehyde. J Agric Food Chem. 2018 Oct 24;66(42):10952-10963. doi: 10.1021/acs.jafc.8b00782. Epub 2018 Oct 11. [PubMed:30269491 ]

Showing NP-Card for Orsellinaldehyde (NP0010751)

MOL for NP0010751 (Orsellinaldehyde)

3D MOL for NP0010751 (Orsellinaldehyde)

3D SDF for NP0010751 (Orsellinaldehyde)

3D-SDF for NP0010751 (Orsellinaldehyde)

PDB for NP0010751 (Orsellinaldehyde)

3D PDB for NP0010751 (Orsellinaldehyde)

SMILES for NP0010751 (Orsellinaldehyde)

INCHI for NP0010751 (Orsellinaldehyde)

Structure for NP0010751 (Orsellinaldehyde)

3D Structure for NP0010751 (Orsellinaldehyde)